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US 12,733,394 B2Granted
Organic light-emitting device
AssigneeSfc Co., Ltd.
InventorsJin-hwi Cho, Se-jin Yu, So-young Shim, Yong-woon Yang
Life of this patent
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Abstract
Disclosed is a highly efficient organic light-emitting device that uses an anthracene derivative having a characteristic structure as a host compound in a light-emitting layer of the organic light-emitting device and includes a capping layer formed using a compound having a characteristic structure in the organic light-emitting device.
Claims20
An organic light-emitting device comprising:
- a first electrode;
- a second electrode facing the first electrode;
- a light-emitting layer interposed between the first electrode and the second electrode;
- and
- a capping layer disposed on one surface of the first electrode or the second electrode which is opposite to a remaining surface of the first electrode or the second electrode that faces the light-emitting layer,
- wherein the light-emitting layer comprises at least one selected from compounds represented by the following [Formula A-1] to [Formula A-6], and
- the capping layer comprises at least one of compounds represented by the following [Formula B] or [Formula C]:
- wherein Ar1 is selected from a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C50 heteroaryl group, and a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group,
- R1 to R14 are identical to or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C50 aryloxy group, a substituted or unsubstituted C1-C30 alkylthioxy group, a substituted or unsubstituted C6-C50 arylthioxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group, a cyano group, a nitro group and a halogen group,
- X is an oxygen atom (O) or a sulfur atom(S),
- L1 is a divalent linker and is a single bond or is selected from a substituted or unsubstituted C6-C50 arylene group, a substituted or unsubstituted C2-C50 heteroarylene group, and a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group, and
- m is an integer from 1 to 3, provided that when m is 2 or more, a plurality of L1 are identical to or different from each other,
- wherein R21 to R23 are identical to or different from each other, and are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C7-C50 arylalkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted silyl group, and a halogen group,
- L21 to L24 are identical to or different from each other, and are each independently a single bond or are selected from are selected from a substituted or unsubstituted C6-C50 arylene group and a substituted or unsubstituted C2-C50 heteroarylene group,
- Ar21 to Ar24 are identical to or different from each other, and are each independently selected from a substituted or unsubstituted C6-C50 aryl group, and a substituted or unsubstituted C2-C50 heteroaryl group,
- n is an integer from 0 to 4, provided that when n is 2 or more, a plurality of aromatic ring structures in ( ) including R23 are identical to or different from each other,
- m1 to m3 are integers from 0 to 4, provided that when each of m1 to m3 is 2 or more, a plurality of each of R21, R22, and R23 are identical to or different from each other, and
- a carbon atom of the aromatic ring, to which R21 to R23 are not bonded, is bonded to hydrogen or deuterium,
- wherein Ar25 to Ar27 are divalent linkers, are identical to or different from each other, and are each independently single bonds or are selected from a substituted or unsubstituted C6-C50 arylene group, a substituted or unsubstituted C2-C50 heteroarylene group, a substituted or unsubstituted C3-C30 cycloalkylene group, and a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group, and
- W's are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, or a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C50 aryloxy group, a substituted or unsubstituted C1-C30 alkylthioxy group, a substituted or unsubstituted C6-C50 arylthioxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group, a nitro group and a halogen group,
- wherein W's are identical to or different from each other, with the proviso that at least one of W's is represented by the following [Formula C-1]:
- wherein R24 to R29 are identical to or different from each other, and are each independently linkers as binding sites to Ar25 to Ar27, or are selected from hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C50 aryloxy group, a substituted or unsubstituted C1-C30 alkylthioxy group, a substituted or unsubstituted C6-C50 arylthioxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group, a cyano group, a nitro group and a halogen group, with the proviso that R24 to R27 are bonded to each other or each of R24 to R27 is bonded to an adjacent substituent to further form an alicyclic or aromatic monocyclic or polycyclic ring, at least one carbon atom of which is substituted with at least one heteroatom selected from nitrogen, oxygen, and sulfur, and
- Q is N, O or S, provided that when Q is O or S, Q does not include R29,
- wherein at least one of R11 to R14 in each of the compounds represented by [Formula A-1] to [Formula A-6] is a substituted or unsubstituted C3-C20 cycloalkyl group.
21 more elements
An organic light-emitting device comprising:
- a first electrode;
- a second electrode facing the first electrode;
- a light-emitting layer interposed between the first electrode and the second electrode;
- and
- a capping layer disposed on one surface of the first electrode or the second electrode which is opposite to a remaining surface of the first electrode or the second electrode that faces the light-emitting layer,
- wherein the light-emitting layer comprises at least one selected from compounds represented by the following [Formula A-1] to [Formula A-6], and
- the capping layer comprises a compound represented by the following [Formula C]:
- wherein Ar1 is selected from a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C50 heteroaryl group, and a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group,
- R1 to R14 are identical to or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C50 aryloxy group, a substituted or unsubstituted C1-C30 alkylthioxy group, a substituted or unsubstituted C6-C50 arylthioxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group, a cyano group, a nitro group and a halogen group,
- X is an oxygen atom (O) or a sulfur atom(S),
- L1 is a divalent linker and is a single bond or is selected from a substituted or unsubstituted C6-C50 arylene group, a substituted or unsubstituted C2-C50 heteroarylene group, and a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group, and
- m is an integer from 1 to 3, provided that when m is 2 or more, a plurality of L1 are identical to or different from each other,
- wherein Ar25 to Ar27 are divalent linkers, are identical to or different from each other, and are each independently single bonds or are selected from a substituted or unsubstituted C6-C50 arylene group, a substituted or unsubstituted C2-C50 heteroarylene group, a substituted or unsubstituted C3-C30 cycloalkylene group, and a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group, and
- W's are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, or a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C50 aryloxy group, a substituted or unsubstituted C1-C30 alkylthioxy group, a substituted or unsubstituted C6-C50 arylthioxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group, a nitro group and a halogen group, wherein W's are identical to or different from each other, with the proviso that at least one of W's is represented by the following [Formula C-1]:
- wherein R24 to R29 are identical to or different from each other, and are each independently linkers as binding sites to Ar25 to Ar27, or are selected from hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C50 aryloxy group, a substituted or unsubstituted C1-C30 alkylthioxy group, a substituted or unsubstituted C6-C50 arylthioxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group, a cyano group, a nitro group and a halogen group, with the proviso that R24 to R27 are bonded to each other or each of R24 to R27 is bonded to an adjacent substituent to further form an alicyclic or aromatic monocyclic or polycyclic ring, at least one carbon atom of which is substituted with at least one heteroatom selected from nitrogen, oxygen, and sulfur, and
- Q is N.
13 more elements
An organic light-emitting device comprising:
- a first electrode;
- a second electrode facing the first electrode;
- a light-emitting layer interposed between the first electrode and the second electrode;
- and
- a capping layer disposed on one surface of the first electrode or the second electrode which is opposite to a remaining surface of the first electrode or the second electrode that faces the light-emitting layer,
- wherein the light-emitting layer comprises at least one selected from compounds represented by the following [Formula A-1] to [Formula A-6], and
- the capping layer comprises a compound represented by the following [Formula B]:
- wherein Ar1 is selected from a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C50 heteroaryl group, and a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group,
- R1 to R14 are identical to or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C50 aryloxy group, a substituted or unsubstituted C1-C30 alkylthioxy group, a substituted or unsubstituted C6-C50 arylthioxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group, a cyano group, a nitro group and a halogen group,
- X is an oxygen atom (O) or a sulfur atom(S),
- L1 is a divalent linker and is a single bond or is selected from a substituted or unsubstituted C6-C50 arylene group, a substituted or unsubstituted C2-C50 heteroarylene group, and a substituted or unsubstituted C3-C50 mixed aliphatic-aromatic ring group, and
- m is an integer from 1 to 3, provided that when m is 2 or more, a plurality of L1 are identical to or different from each other,
- wherein R21 to R23 are identical to or different from each other, and are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C7-C50 arylalkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted silyl group, and a halogen group,
- L21 to L24 are identical to or different from each other, and are each independently a single bond or are selected from are selected from a substituted or unsubstituted C6-C50 arylene group and a substituted or unsubstituted C2-C50 heteroarylene group,
- Ar21 to Ar24 are identical to or different from each other, and are each independently selected from a substituted or unsubstituted C6-C50 aryl group, and a substituted or unsubstituted C2-C50 heteroaryl group,
- n is an integer from 0 to 4, provided that when n is 2 or more, a plurality of aromatic ring structures in ( ) including R23 are identical to or different from each other,
- m1 to m3 are integers from 0 to 4, provided that when each of m1 to m3 is 2 or more, a plurality of each of R21, R22, and R23 are identical to or different from each other, and
- at least one carbon atom of aromatic rings, to which R21 to R23 are bonded, is bonded to deuterium.
15 more elements
Dependencies are inferred from the claim text.